Carisbamate → (R)-Carisbamate

HRID 1940026Notes

Reaction equation

[C:1]([O:4][CH2:5][C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[OH:7])(=[O:3])[NH2:2].C([O:18][CH2:19][C@@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])[OH:21])(=[O:17])N>>[C:1](=[O:3])([OH:17])[OH:4].[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C@@H:20]([OH:21])[CH2:19][OH:18].[C:1]([O:4][CH2:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[OH:7])(=[O:3])[NH2:2]

Participants

Reactant 2

HCID 6918474Carisbamate

HCID 9942577(R)-Carisbamate

Product 2

HCID 9942577(R)-CarisbamateYield 54%

HCID 67679901HCID 67679901, compound

Procedure

(R)-1-o-Chlorophenyl-1,2-ethanediol carbonate was prepared using the same synthetic method described in Example 2, except that (S)-2-carbamoyloxy-1-o-chlorophenylethanol (10.98 g) was used instead of (D/L)-1-m-chlorophenyl-1,2-ethanediol. The crude (R)-2-carbamoyloxy-1-o-chlorophenylethanol prepared in this manner was used in the synthetic method described in Example 6 for (D/L)-1-m-chlorophenyl-1,2-ethanediol carbonate to yield (R)-2-carbamoyloxy-1-o-chlorophenylethanol (4.02 g, yield 54%). An analytically pure sample of (R)-2-carbamoyloxy-1-o-chlorophenylethanol ethanediol (3.35 g, yield 45%, m.p. 133° C., [α]D =-63.9 (c=2.22, methanol)) was obtained by recrystallization from ethyl acetate.

Sources & evidence

ORD record: ord-76ab8b61583548d980ad47ce613ec2f1
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05698588

Reaction notes

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